5H-furan-2-one derivatives for stabilization of organic material

ABSTRACT

A composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation; and b) a compound of formula I (Formula I) (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  are independently from each other H, C 1 -C 8 -alkyl, C 4 -C 8 -cycloalkyl, phenyl, C 1 -C 4 -alkoxy or halogen; n is 1, 2, 3, or 4; and when n is 1 A is —C(=0)-OR′ 1 , —C(=0)-N(R′ 2 )(R′ 3 ), —CN, phenyl, which is unsubstituted or substituted by one or more C 1 -C 8 -alkyl, C 4 -C 8 -alkoxy, C 5 -C 7 -cycloalkyl or halogen, —H or —S0 2 -phenyl; when n is 2 A is —C(=0)-O—Z 1 —O—C(=0)-, —C(=0)-N(R″ 1 )—Z 2 —N(R″ 2 )—C(=0)- or piperazine-N,N′-biscarbonyl.

Organic materials are susceptible to degradation, which can be inducedby heat, light and/or oxidation. For reducing such degradation, numeroussolutions in regard to an incorporation or addition of a stabilizer areproposed.

There is still a need for further technical solutions towardsstabilisation of organic material against the detrimental impact ofheat, light and/or oxidation.

US-A-2003/0083405 discloses inter alia 5H-dihydro-furan-2-onederivatives as antioxidants for stabilization of a polymer.

It has now been found that a specific group of 5H-dihydro-furan-2-onederivatives are suitable for stabilization of organic material againstdegradation by heat, light and/or oxidation.

The present invention relates to a composition, which comprises

-   a) an organic material susceptible to oxidative, thermal or    light-induced degradation; and-   b) a compound of formula I

wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is    unsubstituted or substituted by one or more C₁-C₈-alkyl,    C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl),    3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl),    1,4,7-triazaheptane-1,4,7-tricarbonyl,    1,4,8-triazaoctane-1,4,8-tricarbonyl or    1,5,9-triazanonane-1,5,9-tricarbonyl;    when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl),    1,4,7,10-tetraazadecane-1,4,7,10-tetracarbonyl,    1,4,8,11-tetraazaundecane-1,4,8,11-tetracarbonyl or    1,5,8,12-tetraazadodecane-1,5,8,12-tetracarbonyl;-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,    which is substituted by a hydroxyl group, C₆-C₁₀-aryl,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms,    hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,    C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

A compound of formula I possess at least one asymmetric carbon atom,i.e. the carbon atom at the 5-position of the furan-2-one ring, whichresults in enantiomers. The invention relates to any one of theseenantiomers or mixtures thereof. Several combinations of substituents atformula I lead to the presence of at least two asymmetric carbon atoms,which results in diastereomers. The invention relates to any one ofthese diastereomers or mixtures thereof.

C₁-C₂₂-alkyl is linear or branched and for example methyl, ethyl,n-propyl, 1-methyl-ethyl, n-butyl, 1-methyl-propyl, 2-methyl-propyl,1,1-dimethyl-ethyl, n-pentyl, 1-methyl-butyl, 3-methyl-butyl, n-hexyl,1-methyl-pentyl, 2-methyl-pentyl, 4-methyl-pentyl, 2-ethyl-butyl,n-heptyl, 1-methyl-hexyl, n-octyl, 1-methyl-heptyl, 2-ethyl-hexyl,5,5-dimethyl-hexyl, 1,1,3,3-tetramethyl-butyl, n-nonyl, 2-ethyl-heptyl,n-decyl, undecyl, n-dodecyl, tridecyl, tetradecyl, pentadecyl,n-hexadecyl or n-octadecyl. Preferred is C₁-C₁₈-alkyl, in particularC₁-C₁₂-alkyl, especially C₁-C₈-alkyl, very especially C₁-C₄-alkyl.

C₂-C₁₈-alkenyl is linear or branched and for example vinyl, allyl, Z- orE-but-2-ene-yl, Z- or E-but-3-ene-yl, Z- or E-pent-2-ene-yl,pent-4-ene-yl, Z- or E-2-methyl-but-2-ene-yl, Z- orE-3-methyl-but-3-ene-yl, Z- or E-hex-1-ene-yl, Z- or E-hexadec-9-ene-ylor Z- or E-octadec-9-ene-yl.

C₃-C₁₂-alkine-yl is for example propargyl, but-2-ine-yl orundec-11-ine-yl.

C₄-C₈-cycloalkyl is for example cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl or cyclooctyl. Preferred is C₅-C₇-cycloalkyl, in particularcyclohexyl.

C₄-C₈-cycloalkyl, which is substituted by one to three C₁-C₄-alkyl, isfor example 3,4-dimethyl-cyclopentyl, 4-methyl-cyclohexyl,2-methyl-cyclohexyl, 3,5-dimethyl-cyclohexyl or4-(1-methyl-ethyl)-cyclohexyl or 5-methyl-2-(1-methyl-ethyl)-cyclohexyl.

C₆-C₁₀-aryl is for example phenyl, 2-methyl-phenyl, 3-methyl-phenyl,4-methyl-phenyl, 2,4-dimethyl-phenyl, 4-(1,1-dimethylethyl)-phenyl,biphenyl-4-yl, napthalen-1-yl or napthalen-2-yl. Preferred is phenyl.

Bicyclic or tricyclic C₅-C₂₀-alkyl is for example2-methyl-bicyclo[2.2.1]heptane-1′-yl,1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl, adamantane-yl,1-methyl-adamantane-1′-yl or 1,3-dimethyl-adamantane-1′-yl.

C₄-C₈-cycloalkyl-C₁-C₄-alkyl is for example 2-(cyclopentyl)-ethyl,cyclohexyl-methyl, 2-(cyclohexyl)-ethyl, 2-(cyclohexyl)-1-methyl-ethylor (cycloheptyl)-methyl.

C₆-C₁₄-aryl-C₁-C₄-alkyl is for example benzyl, 4-methyl-benzyl,2-phenyl-ethyl, 3,5-dimethylbenzyl, 1-phenyl-1,1-dimethyl-methyl,3-phenyl-propyl, 3-phenyl-2-methyl-propyl, 3,5-di-tert-butyl-benzyl orbiphenyl-4-yl-methyl.

C₂-C₁₂-alkyl, which is substituted by one or more hydroxyl groups, isfor example 2-hydroxy-ethyl, 3-hydroxy-propyl, 2-hydroxy-2-methyl-ethyl,2,2-dimethyl-3-hydroxy-propyl, 4-hydroxy-butyl, 6-hydroxy-hexyl,2,3-dihydroxy-propyl, 2-hydroxy-butyl, 2-hydroxy-hexyl,1,3-dihydroxy-propane-2-yl, 2,3,4,5-tetrahydroxy-pentyl or2,3,4,5,6-pentahydroxy-hexyl. Preferred is C₂-C₈-alkyl, which issubstituted by one hydroxyl group. Preferred in particular is2-hydroxy-ethyl or 2-hydroxy-2-methyl-ethyl.

C₁-C₈-alkoxy is for example methoxy, ethoxy, n-propoxy, 1-methyl-ethoxy,n-butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy,n-pentoxy, 1-methyl-butoxy, 2-methyl-butoxy, 3-methyl-butoxy,n-hexane-oxy, n-heptane-oxy, n-octane-oxy or 1-methyl-heptane-oxy.C₁-C₄-alkoxy is preferred.

Phenyl, which is unsubstituted or substituted by one or moreC₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, is for examplephenyl, 2-methyl-phenyl, 3-methyl-phenyl, 3,5-dimethyl-phenyl,4-methyl-phenyl, 3-(1-methyl-propyl)-phenyl, 4-(1-methyl-propyl)-phenyl,4-(1,1-dimethyl-ethyl)-phenyl, 4-(1,1,3,3-tetramethyl-butyl)-phenyl,4-cyclohexyl-phenyl, biphenyl-4-yl, 2-methoxy-phenyl, 3-methoxy-phenyl,4-methoxy-phenyl, 4-ethoxy-phenyl, 2-chloro-phenyl, 3-chloro-phenyl,4-chloro-phenyl or 4-bromo-phenyl. Preferred is phenyl, which isunsubstituted or substituted by one C₁-C₈-alkyl, C₁-C₄-alkoxy,C₅-C₇-cycloalkyl or halogen. Preferred is phenyl, which isunsubstituted.

C₄-C₁₂-alkyl, which is interrupted by one or more oxygen atoms, is forexample 2-ethoxy-ethyl, 2-(2-methoxy-ethoxy)-ethyl, 2-n-butoxy-ethyl,2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl,2-[2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy]-ethyl,2-(2-methoxy-1-methyl-ethoxy)-1-methyl-ethyl, 3-(n-propoxy)-propyl,2-(2-hydroxy-ethoxy)-ethyl,2-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-ethyl or2-[2-(2-hydroxy-2-methyl-ethoxy)-2-methyl-ethoxy]-2-methyl-ethyl.

C₄-C₁₆-alkyl, which is interrupted by one sulfur atom, is for example3-thiaundecyl or 3-thiapentadecyl.

Halogen is for example a chlorine atom, a bromine atom or iodine atom.Preferred is a chlorine atom.

C₂-C₁₂-alkylene is for example ethylene, 1-methyl-ethane-1,2-diyl,n-propylene, n-butylene, 2-methyl-butane-1,4-diyl, hexamethylene ordecane-1,10-diyl.

C₄-C₈-cycloalkylene is for example cyclopentane-1,2-diyl,cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cyclohexane-1,2-diyl,cyclooctane-1,2-diyl or cycloheptane-1,3-diyl.

C₆-C₁₄-arylene is for example 1,3-phenylene, 1,4-phenylene,2,3-dimethyl-benzene-1,4-diyl, biphenyl-4,4′-diyl, naphtalene-2,6-diylor naphthalene-1,4-diyl.

C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene) is for examplecyclopentane-1,3-bismethylene, cyclohexane-1,4-bismethylene,cyclohexane-1,3-bismethylene, cyclohexane-1,4-bisethylene orcyclohexane-1,4-bis(1-methyl-ethane-1,2-diyl).

C₆-C₁₄-arene-bis-(C₁-C₄-alkylene) is for examplebenzene-1,3-bismethylene, benzene-1,4-bismethylene,napthaline-1,4-bismethylene, napthaline-2,6-bismethylene,5-methyl-benzene-1,3-bismethylene,5-tert-butyl-benzene-1,3-bismethylene, benzene-1,4-bisethylene,benzene-1,4-bis-(1-methyl-ethan-1,2-diyl) or biphenyl-4,4′-bismethylene.

C₃-C₆-alkylene, which is substituted by one or more hydroxyl groups, isfor example 2-hydroxy-propane-1,3-diyl, 1-hydroxymethyl-ethane-1,2-diyl,2,3,4-trihydroxypentane-1,5-diyl, 2,3,4-trihydroxyhexane-1,6-diyl or2,3,4,5-tetrahydroxy-hexane-1,6-diyl.

C₄-C₁₂-alkylene, which is interrupted by one or more oxygen atoms, isfor example 2-ethoxyethane-1,2′-diyl, —(CH₂CH₂—O)₂—CH₂CH₂—,—(CH₂CH₂—O)₃—CH₂CH₂—, —CH(CH₃)CH₂—O—CH(CH₃)CH₂—,—[CH(CH₃)CH₂—O]₂—CH(CH₃)CH₂—, —CH₂CH₂CH₂CH₂—O—CH₂CH₂CH₂CH₂— or—(CH₂CH₂CH₂CH₂—O)₂—CH₂CH₂CH₂CH₂—.

C₄-C₈-alkylene, which is interrupted by one sulfur atom, is for example—CH₂CH₂—S—CH₂CH₂—, —CH₂CH₂CH₂—S—CH₂CH₂CH₂— or—CH(CH₃)CH₂—S—CH₂—CH(CH₃)—.

3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl is for exampleCH₂CH₂—N(CH₃)—CH₂CH₂— or —CH₂CH₂—N(CH₂—C(CH₃)₂—CH₂—CH₃)—CH₂CH₂—.

4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl is for exampleCH₂CH₂CH₂—N(CH₃)—CH₂CH₂CH₂— or—CH₂CH₂—N(CH₂—C(CH₃)₂—CH₂—CH₃)—CH₂CH₂CH₂—.

A 5-, 6- or 7-membered saturated heterocycle is for example pyrrolidine,piperidine, azepane, morpholine or 2,6-dimethyl-morpholine.

The sign ‘star’ (=−*) indicates the free bonding valence of the carbonatom at the depicted radicals below.

Hexahydro-furo[3,2-b]furane-3,6-diyl is a divalent radical as depicted:

Piperazine-N,N′-biscarbonyl is a divalent radical as depicted:

1-Ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl is a divalent radical asdepicted:

C₃-C₁₂-alkane-tri-(oxycarbonyl) is a trivalent radical and for examplepropane-1,2,3-tri-(oxycarbonyl) as depicted:

2-methyl-propane-1,2,3-tri-(oxycarbonyl) as depicted:

2-methyl-butane-1,2,1′-tri-(oxycarbonyl) as depicted:

2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl) as depicted:

or

2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl) as depicted:

3-Ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl) is a trivalent radical asdepicted:

1,4,7-Triazaheptane-1,4,7-tricarbonyl is a trivalent radical asdepicted:

1,4,8-Triazaoctane-1,4,8-tricarbonyl is a trivalent radical as depicted:

1,5,9-Triazanonane-1,5,9-tricarbonyl is a trivalent radical as depicted:

C₄-C₁₆-alkane-tetra-(oxycarbonyl) is a tetravalent radical and forexample 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl) as depicted:

butane-1,2,3,4-tetra-(oxycarbonyl) as depicted:

hexane-1,3,4,6-tetra-(oxycarbonyl) as depicted:

or

octane-1,3,6,8-tetra-(oxycarbonyl) as depicted:

1,4,7,10-Tetraazadecane-1,4,7,10-tetracarbonyl is a tetravalent radicalas depicted:

1,4,8,11-Tetraazaundecane-1,4,8,11-tetracarbonyl is a tetravalentradical as depicted:

1,5,8,12-Tetraazadodecane-1,5,8,12-tetracarbonyl is a tetravalentradical as depicted:

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen, with the proviso that at least R₁ or R₅ is H and at least    R₆ or R₁₀ is H.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄ and R₅ are independently from each other H,    C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen;-   R₆ is R₁; R₇ is R₂; R₈ is R₃; R₉ is R₄ and R₁₀ is R₅.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄ and R₅ are independently from each other H,    C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen, with    the proviso that at least R₁ is H;-   R₆ is R₁; R₇ is R₂; R₈ is R₃; R₉ is R₄ and R₁₀ is R₅.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, methyl or methoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and-   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl,    C₁-C₄-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and-   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl, phenyl    or C₁-C₄-alkoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and-   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl or    C₁-C₄-alkoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and-   R₃ and R₈ are independently from each other H or methoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H.

Preferred is a compound of formula I, wherein

-   R′₃ is H; and-   R″₂ and R″₃ are H.

Preferred is a compound of formula I, wherein

-   n is 1, 2 or 3.

Preferred is a compound of formula I, wherein

-   n is 1 or 2.

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is    substituted by one or more C₁-C₈-alkyl, C₁-C₄-alkoxy,    C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl.

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, —H or —SO₂-phenyl.

Preferred is a compound of formula I, wherein

-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl);-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl).

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁, —CN, phenyl, which is unsubstituted or substituted    by one or more C₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or    halogen, —H or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl);-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl).

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is    unsubstituted or substituted by one or more C₁-C₈-alkyl,    C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)— or —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)—;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl) or    3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl);-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl);-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkinyl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,    which is substituted by a hydroxyl group,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms,    hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,    C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁ or —C(═O)—N(R′₂)(R′₃);-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl);-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl);-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,    which is substituted by a hydroxyl group,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is    interrupted by a sulfur atom; and-   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,    C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I,wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is    unsubstituted or substituted by one to three C₁-C₈-alkyl or    C₁-C₄-alkoxy, —H or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is propane-1,2,3-tri-(oxycarbonyl),    2-methyl-propane-1,2,3-tri-(oxycarbonyl),    2-methyl-butane-1,2,1′-tri-(oxycarbonyl),    2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl),    2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl),    3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl);-   when n is 4-   A is 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl);-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, phenyl or C₁-C₄-alkoxy with the proviso    that at least R₁ or R₅ is H and at least R₆ or R₁₀ is H;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is    unsubstituted or substituted by one C₁-C₄-alkyl,    C₅-C₇-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₀-aryl-C₁-C₄-alkyl, C₄-C₁₂-alkyl,    which is interrupted by one or more oxygen atoms,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted or    substituted by one C₁-C₄-alkyl, C₅-C₁₀-aryl,    C₅-C₇-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₀-aryl-C₁-C₄-alkyl,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    pyrrolidine, a piperidine or a morpholine;-   R″₁ and R″₂ independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted or    substituted by one C₁-C₄-alkyl, C₅-C₇-cycloalkyl-C₁-C₄-alkyl,    C₆-C₁₀-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene,    C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₀-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene, C₆-C₁₄-arylene,    C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₉-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I,wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is    unsubstituted or substituted by one or two C₁-C₈-alkyl or    C₁-C₄-alkoxy, —H or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is propane-1,2,3-tri-(oxycarbonyl),    2-methyl-propane-1,2,3-tri-(oxycarbonyl),    2-methyl-butane-1,2,1′-tri-(oxycarbonyl),    2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl),    2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl);-   when n is 4-   A is 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl);-   n is 1, 2, 3 or 4;-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H;

R₃ and R₈ are independently from each other H, C₁-C₈-alkyl,C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen;

-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is    unsubstituted, C₅-C₇-cycloalkyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,    C₄-C₁₂-alkyl, which is interrupted by one or more oxygen atoms,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted,    C₅-C₁₀-aryl, C₅-C₇-cycloalkyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    pyrrolidine, a piperidine or a morpholine;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted,    C₅-C₇-cycloalkyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene,    C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),    benzene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is substituted    by one or more hydroxyl groups, C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene, C₆-C₁₄-arylene,    C₅-C₇-cycloalkane-bis(C₁-C₄-alkylene), benzene-bis-(C₁-C₄-alkylene),    C₄-C₁₂-alkylene, which is interrupted by one or more oxygen atoms,    3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I,wherein

-   n is 1,-   A is —CN, phenyl or —H; and-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen.

Preferred is a composition, which comprise a compound of formula I,wherein at formula I

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, —H or    —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—;-   n is 1 or 2;-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H;-   R₃ and R₈ are independently from each other H or C₁-C₄-alkoxy;-   R′₁ is H, C₁-C₁₂-alkyl, C₅-C₇-cycloalkyl, which is unsubstituted,    phenyl-C₁-C₄-alkyl,    1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₁₂-alkyl,    C₅-C₇-cycloalkyl, which is unsubstituted, C₆-C₁₀-aryl,    phenyl-C₁-C₄-alkyl,    1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    pyrrolidine, a piperidine or a morpholine; and-   Z₁ is C₅-C₇-cycloalkylene.

Preferred is a composition, which comprise a compound of formula I,wherein

-   when n is 1-   A is —C(═O)—OCH₃, —CN, phenyl or —H;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—;-   n is 1 or 2;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H; and-   Z₁ is cyclo-hexane-1,4-diyl.

The organic material of the present invention is susceptible tooxidative, thermal or light-induced degradation.

Examples of an organic material are:

-   1. Polymers of monoolefins and diolefins, for example polypropylene,    polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene,    polyvinylcyclohexane, polyisoprene or polybutadiene, as well as    polymers of cycloolefins, for instance of cyclopentene or    norbornene, polyethylene (which optionally can be crosslinked), for    example high density polyethylene (HDPE), high density and high    molecular weight polyethylene (HDPE-HMW), high density and ultrahigh    molecular weight polyethylene (HDPE-UHMW), medium density    polyethylene (MDPE), low density polyethylene (LDPE), linear low    density polyethylene (LLDPE), (VLDPE) and (ULDPE).

Polyolefins, i.e. the polymers of monoolefins exemplified in thepreceding paragraph, preferably polyethylene and polypropylene, can beprepared by different, and especially by the following, methods:

-   -   a) radical polymerisation (normally under high pressure and at        elevated temperature).    -   b) catalytic polymerisation using a catalyst that normally        contains one or more than one metal of groups IVb, Vb, VIb or        VIII of the Periodic Table. These metals usually have one or        more than one ligand, typically oxides, halides, alcoholates,        esters, ethers, amines, alkyls, alkenyls and/or aryls that may        be either π- or σ-coordinated. These metal complexes may be in        the free form or fixed on substrates, typically on activated        magnesium chloride, titanium(III) chloride, alumina or silicon        oxide. These catalysts may be soluble or insoluble in the        polymerisation medium. The catalysts can be used by themselves        in the polymerisation or further activators may be used,        typically metal alkyls, metal hydrides, metal alkyl halides,        metal alkyl oxides or metal alkyloxanes, said metals being        elements of groups Ia, IIa and/or IIIa of the Periodic Table.        The activators may be modified conveniently with further ester,        ether, amine or silyl ether groups. These catalyst systems are        usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta),        TNZ (DuPont), metallocene or single site catalysts (SSC).

-   2. Mixtures of the polymers mentioned under 1), for example mixtures    of polypropylene with polyisobutylene, polypropylene with    polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of    different types of polyethylene (for example LDPE/HDPE).

-   3. Copolymers of monoolefins and diolefins with each other or with    other vinyl monomers, for example ethylene/propylene copolymers,    linear low density polyethylene (LLDPE) and mixtures thereof with    low density polyethylene (LDPE), propylene/but-1-ene copolymers,    propylene/isobutylene copolymers, ethylene/but-1-ene copolymers,    ethylene/hexene copolymers, ethylene/methylpentene copolymers,    ethylene/heptene copolymers, ethylene/octene copolymers,    ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin    copolymers (e.g. ethylene/norbornene like COC), ethylene/1-olefins    copolymers, where the 1-olefin is generated in-situ;    propylene/butadiene copolymers, isobutylene/isoprene copolymers,    ethylene/vinylcyclohexene copolymers, ethylene/alkyl acrylate    copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl    acetate copolymers or ethylene/acrylic acid copolymers and their    salts (ionomers) as well as terpolymers of ethylene with propylene    and a diene such as hexadiene, dicyclopentadiene or    ethylidene-norbornene; and mixtures of such copolymers with one    another and with polymers mentioned in 1) above, for example    polypropylene/ethylenepropylene copolymers, LDPE/ethylene-vinyl    acetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers    (EAA), LLDPE/EVA, LLDPE/EAA and alternating or random    polyalkylene/carbon monoxide copolymers and mixtures thereof with    other polymers, for example polyamides.

A special copolymer of two monoolefins is a pipe grade polypropylenerandom copolymer, which is obtainable from the polymerization of morethan 90% by weight of propylene and of less than 10% by weight,typically between 2 and 6% by weight, of ethylene.

-   4. Hydrocarbon resins (for example C₅-C₉) including hydrogenated    modifications thereof (e.g. tackifiers) and mixtures of    polyalkylenes and starch. Homopolymers and copolymers from 1.)-4.)    may have any stereostructure including syndiotactic, isotactic,    hemi-isotactic or atactic; where atactic polymers are preferred.    Stereoblock polymers are also included.-   5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).-   6. Aromatic homopolymers and copolymers derived from vinyl aromatic    monomers including styrene, α-methylstyrene, all isomers of vinyl    toluene, especially p-vinyl-toluene, all isomers of ethyl styrene,    propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl    anthracene, and mixtures thereof. Homopolymers and copolymers may    have any stereostructure including syndiotactic, isotactic,    hemi-isotactic or atactic; where atactic polymers are preferred.    Stereoblock polymers are also included.-   6a. Copolymers including aforementioned vinyl aromatic monomers and    comonomers selected from ethylene, propylene, dienes, nitriles,    acids, maleic anhydrides, maleimides, vinyl acetate and vinyl    chloride or acrylic derivatives and mixtures thereof, for example    styrene/butadiene, styrene/acrylonitrile, styrene/ethylene    (interpolymers), styrene/alkyl methacrylate, styrene/butadiene/alkyl    acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic    anhydride, styrene/acrylonitrile/methyl acrylate; mixtures of high    impact strength of styrene copolymers and another polymer, for    example a polyacrylate, a diene polymer or an    ethylene/propylene/diene terpolymer; and block copolymers of styrene    such as styrene/butadiene/styrene, styrene/isoprene/styrene,    styrene/ethylene/butylene/styrene or    styrene/ethylene/propylene/styrene.-   6b. Hydrogenated aromatic polymers derived from hydrogenation of    polymers mentioned under 6.), especially including    polycyclohexylethylene (PCHE) prepared by hydrogenating atactic    polystyrene, often referred to as polyvinylcyclohexane (PVCH).-   6c. Hydrogenated aromatic polymers derived from hydrogenation of    polymers mentioned under 6a.).

Homopolymers and copolymers may have any stereostructure includingsyndiotactic, isotactic, hemi-isotactic or atactic; where atacticpolymers are preferred. Stereoblock polymers are also included.

-   7. Graft copolymers of vinyl aromatic monomers such as styrene or    α-methylstyrene, for example styrene on polybutadiene, styrene on    polybutadiene-styrene or polybutadiene-acrylonitrile copolymers;    styrene and acrylonitrile (or methacrylonitrile) on polybutadiene;    styrene, acrylonitrile and methyl methacrylate on polybutadiene;    styrene and maleic anhydride on polybutadiene; styrene,    acrylonitrile and maleic anhydride or maleimide on polybutadiene;    styrene and maleimide on polybutadiene; styrene and alkyl acrylates    or methacrylates on polybutadiene; styrene and acrylonitrile on    ethylene/propylene/diene terpolymers; styrene and acrylonitrile on    polyalkyl acrylates or polyalkyl methacrylates, styrene and    acrylonitrile on acrylate/butadiene copolymers, as well as mixtures    thereof with the copolymers listed under 6), for example the    copolymer mixtures known as ABS, MBS, ASA or AES polymers.-   8. Halogen-containing polymers such as polychloroprene, chlorinated    rubbers, chlorinated and brominated copolymer of    isobutylene-isoprene (halobutyl rubber), chlorinated or    sulfochlorinated polyethylene, copolymers of ethylene and    chlorinated ethylene, epichlorohydrin homo- and copolymers,    especially polymers of halogen-containing vinyl compounds, for    example polyvinyl chloride, polyvinylidene chloride, polyvinyl    fluoride, polyvinylidene fluoride, as well as copolymers thereof    such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl    acetate or vinylidene chloride/vinyl acetate copolymers.-   9. Polymers derived from α,β-unsaturated acids and derivatives    thereof such as polyacrylates and polymethacrylates; polymethyl    methacrylates, polyacrylamides and polyacrylonitriles,    impact-modified with butyl acrylate.-   10. Copolymers of the monomers mentioned under 9) with each other or    with other unsaturated monomers, for example acrylonitrile/butadiene    copolymers, acrylonitrite/alkyl acrylate copolymers,    acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide    copolymers or acrylonitrile/alkyl methacrylate/butadiene    terpolymers.-   11. Polymers derived from unsaturated alcohols and amines or the    acyl derivatives or acetals thereof, for example polyvinyl alcohol,    polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl    maleate, polyvinyl butyral, polyallyl phthalate or polyallyl    melamine; as well as their copolymers with olefins mentioned in 1)    above.-   12. Homopolymers and copolymers of cyclic ethers such as    polyalkylene glycols, polyethylene oxide, polypropylene oxide or    copolymers thereof with bisglycidyl ethers.-   13. Polyacetals such as polyoxymethylene and those polyoxymethylenes    which contain ethylene oxide as a comonomer; polyacetals modified    with thermoplastic polyurethanes, acrylates or MBS.-   14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene    oxides with styrene polymers or polyamides.-   15. Polyurethanes, for example polyurethanes synthesized from a    polyol and an aliphatic or aromatic polyisocyanate such as    polyurethanes derived from hydroxyl-terminated polyethers,    polyesters or polybutadienes on the one hand and aliphatic or    aromatic polyisocyanates on the other, as well as precursors    thereof.

Hydroxyl-terminated polyethers are known and are prepared, for example,by polymerizing epoxides such as ethylene oxide, propylene oxide,butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin withthemselves, for example in the presence of BF₃, or by addition reactionof these epoxides, alone or as a mixture or in succession, with startingcomponents containing reactive hydrogen atoms, such as water, alcohols,ammonia or amines, for example ethylene glycol, propylene 1,3- and1,2-glycol, trimethylolpropane, 4,4′-dihydroxydiphenylpropane, aniline,ethanolamine or ethylenediamine. Sucrose polyethers are also suitable inaccordance with the invention. In many cases preference is given tothose polyethers which predominantly (up to 90% by weight, based on allthe OH groups present in the polyether) contain primary OH groups.Furthermore, polyethers modified by vinyl polymers, as are formed, forexample, by polymerizing styrene and acrylonitrile in the presence ofpolyethers, are suitable, as are polybutadienes containing OH groups.

In particular, a polyol compound has a molecular weight of 400-10000,especially 800 to 10000, and is a polyhydroxy compound, especiallycontaining from 2 to 8 hydroxyl groups, especially from 2 to 4.

Suitable polyisocyanates are aliphatic or aromatic, for example ethylenediisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylenediisocyanate, 1,12-dodecane diisocyanate, cyclobutane 1,3-diisocyanate,cyclohexane 1,3- and -1,4-diisocyanate and also any desired mixtures ofthese isomers,1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and2,6-hexahydrotolylene diisocyanate and also any desired mixtures ofthese isomers, hexahydro-1,3- and/or -1,4-phenylene diisocyanate,perhydro-2,4′- and/or -4,4′-diphenylmethanediisocyanate, 1,3- and1,4-phenylene diisocyanate, 2,4- and 2,6-tolylene diisocyanate, and alsoany desired mixtures of these isomers, diphenylmethane 2,4′- and/or-4,4′-diisocyanate, naphthylene 1,5-diisocyanate, triphenylmethane4,4′,4″-triisocyanate, polyphenyl-polymethylene polyisocyanates as areobtained by aniline-formaldehyde condensation followed byphosgenization, m- and p-isocyanatophenylsulfonyl isocyanates,perchlorinated aryl polyisocyanates, polyisocyanates containingcarbodiimide groups, polyisocyanates containing allophanate groups,polyisocyanates containing isocyanurate groups, polyisocyanatescontaining urethane groups, polyisocyanates containing acylated ureagroups, polyisocyanates containing biuret groups, polyisocyanatescontaining ester groups, reaction products of the abovementionedisocyanates with acetals, and polyisocyanates containing polymeric fattyacid radicals.

It is also possible to employ the isocyanate group-containingdistillation residues, as they are or dissolved in one or more of theabovementioned polyisocyanates, which are obtained in the course of theindustrial preparation of isocyanates. It is additionally possible touse any desired mixtures of the abovementioned polyisocyanates.

Preferred are 2,4- or 2,6-tolylene diisocyanate and any desired mixturesof these isomers (“TDI”), polyphenyl-polymethylene-polyisocyanates asprepared by aniline-formaldehyde condensation followed by phosgenization(“crude MDI”) or polyisocyanates containing carbodiimide, urethane,allophanate, isocyanurate, urea or biuret groups (“modifiedpolyisocyanates”).

The polyurethanes can be homogeneous polyurethanes or cellular.

-   16. Polyamides and copolyamides derived from diamines and    dicarboxylic acids and/or from aminocarboxylic acids or the    corresponding lactams, for example polyamide 4, polyamide 6,    polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide    12, aromatic polyamides starting from m-xylene diamine and adipic    acid; polyamides prepared from hexamethylenediamine and isophthalic    or/and terephthalic acid and with or without an elastomer as    modifier, for example poly-2,4,4,-trimethylhexamethylene    terephthalamide or poly-m-phenylene isophthalamide; and also block    copolymers of the aforementioned polyamides with polyolefins, olefin    copolymers, ionomers or chemically bonded or grafted elastomers; or    with polyethers, e.g. with polyethylene glycol, polypropylene glycol    or polytetramethylene glycol; as well as polyamides or copolyamides    modified with EPDM or ABS; and polyamides condensed during    processing (RIM polyamide systems).-   17. Polyureas, polyimides, polyamide-imides, polyetherimides,    polyesterimides, polyhydantoins and polybenzimidazoles.-   18. Polyesters derived from dicarboxylic acids and diols and/or from    hydroxycarboxylic acids or the corresponding lactones or lactides,    for example polyethylene terephthalate, polybutylene terephthalate,    poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene    naphthalate and polyhydroxybenzoates as well as copolyether esters    derived from hydroxyl-terminated polyethers, and also polyesters    modified with polycarbonates or MBS. Copolyesters may comprise, for    example—but are not limited to—polybutylenesuccinate/terephtalate,    polybutyleneadipate/terephthalate,    polytetramethyleneadipate/terephthalate,    polybutylensuccinate/adipate, polybutylensuccinate/carbonate,    poly-3-hydroxybutyrate/octanoate copolymer,    poly-3-hydroxybutyrate/hexanoate/decanoate terpolymer. Furthermore,    aliphatic polyesters may comprise, for example—but are not limited    to—the class of poly(hydroxyalkanoates), in particular,    poly(propiolactone), poly(butyrolactone), poly(pivalolactone),    poly(valerolactone) and poly(caprolactone), polyethylenesuccinate,    polypropylenesuccinate, polybutylenesuccinate,    polyhexamethylenesuccinate, polyethyleneadipate,    polypropyleneadipate, polybutyleneadipate, polyhexamethyleneadipate,    polyethyleneoxalate, polypropyleneoxelate, polybutyleneoxalate,    polyhexamethyleneoxalate, polyethylenesebacate,    polypropylenesebacate, polybutylenesebacate and polylactic acid    (PLA) as well as corresponding polyesters modified with    polycarbonates or MBS. The term “polylactic acid (PLA)” designates a    homo-polymer of preferably poly-L-lactide and any of its blends or    alloys with other polymers; a co-polymer of lactic acid or lactide    with other monomers, such as hydroxy-carboxylic acids, like for    example glycolic acid, 3-hydroxy-butyric acid, 4-hydroxy-butyric    acid, 4-hydroxy-valeric acid, 5-hydroxy-valeric acid,    6-hydroxy-caproic acid and cyclic forms thereof; the terms “lactic    acid” or “lactide” include L-lactic acid, D-lactic acid, mixtures    and dimers thereof, i.e. L-lactide, D-lactide, meso-lacide and any    mixtures thereof.-   19. Polycarbonates and polyester carbonates.-   20. Polyketones.-   21. Polysulfones, polyether sulfones and polyether ketones.-   22. Crosslinked polymers derived from aldehydes on the one hand and    phenols, ureas and melamines on the other hand, such as    phenol/formaldehyde resins, urea/formaldehyde resins and    melamine/formaldehyde resins.-   23. Drying and non-drying alkyd resins.-   24. Unsaturated polyester resins derived from copolyesters of    saturated and unsaturated dicarboxylic acids with polyhydric    alcohols and vinyl compounds as crosslinking agents, and also    halogen-containing modifications thereof of low flammability.-   25. Crosslinkable acrylic resins derived from substituted acrylates,    for example epoxy acrylates, urethane acrylates or polyester    acrylates.-   26. Alkyd resins, polyester resins and acrylate resins crosslinked    with melamine resins, urea resins, isocyanates, isocyanurates,    polyisocyanates or epoxy resins.-   27. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic,    heterocyclic or aromatic glycidyl compounds, e.g. products of    diglycidyl ethers of bisphenol A and bisphenol F, which are    crosslinked with customary hardeners such as anhydrides or amines,    with or without accelerators.-   28. Natural polymers such as cellulose, rubber, gelatin and    chemically modified homologous derivatives thereof, for example    cellulose acetates, cellulose propionates and cellulose butyrates,    or the cellulose ethers such as methyl cellulose; as well as rosins    and their derivatives.-   29. Blends of the aforementioned polymers (polyblends), for example    PP/EPDM, polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS,    PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic    PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA    6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or    PBT/PET/PC.-   30. Naturally occurring and synthetic organic materials which are    pure monomeric compounds or mixtures of such compounds, for example    mineral oils, animal and vegetable fats, oil and waxes, or oils,    fats and waxes based on synthetic esters (e.g. phthalates, adipates,    phosphates or trimellitates) and also mixtures of synthetic esters    with mineral oils in any weight ratios, typically those used as    spinning compositions, as well as aqueous emulsions of such    materials.-   31. Aqueous emulsions of natural or synthetic rubber, e.g. natural    latex or latices of carboxylated styrene/butadiene copolymers.

A polymer can be natural, semi-synthetic or synthetic. A natural polymeris isolated from a natural source without further syntheticmodifications. A synthetic polymer does not contain a polymer partisolated from a natural source. A semi-synthetic polymer contains atleast one natural polymer part, wherein the natural polymer part can besynthetically modified and/or reacted with monomers to form thesemi-synthetic polymer.

A polymer can be thermoplastic, i.e. it can be shaped into a new form atan elevated temperature, for example at a temperature in the range from150° C. to 340° C.

Preferred is a composition, which comprises as component a) an organicmaterial, wherein the organic material is selected from the groupconsisting of a polymer, a wax, a mineral oil and a fat, and a componentb).

Preferred is a composition, which comprises as component a) a polymer,in particular a semi-synthetic or synthetic polymer, and as component b)a compound of formula I.

Preferred is a composition, which comprises as component a) asemi-synthetic or synthetic polymer.

Preferred is a composition, which comprises as component a) athermoplastic polymer.

Preferred is a composition, which comprises as component a) a polymer,which is synthetic and thermoplastic.

Preferred is a composition, which comprises as component a) apolyolefin, a polyether polyol or a polyurethane.

The employed amount of component b) in regard to component a) varieswith the particular organic material and the desired degree ofprotection.

Preferred is a composition, which comprises a component a) and acomponent b), wherein component b) is contained in an amount of 0.0005%to 10%, in particular from 0.001 to 2%, especially from 0.005 to 1%,based on the weight of component a).

Optionally, a composition comprising a component a) and a component b)contains as component c) a further additive.

A further additive can be selected from the following list:

1. Antioxidants

-   1.1. Alkylated monophenols, for example    2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol,    2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,    2,6-di-tert-butyl-4-isobutylphenol,    2,6-dicyclopentyl-4-methylphenol,    2-(α-methylcyclohexyl)-4,6-dimethylphenol,    2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,    2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are    linear or branched in the side chains, for example    2,6-di-nonyl-4-methylphenol,    2,4-dimethyl-6-(1′-methyl-undec-1′-yl)phenol,    2,4-dimethyl-6-(1′-methyl heptadec-1′-yl) phenol,    2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol,    2,4-dimethyl-6-(1′-methyl-1′-tetradecyl-methyl)-phenol and mixtures    thereof.-   1.2. Alkylthiomethylphenols, for example    2,4-dioctylthiomethyl-6-tert-butylphenol,    2,4-dioctylthiomethyl-6-methylphenol,    2,4-dioctylthiomethyl-6-ethylphenol,    2,6-di-dodecyl-thiomethyl-4-nonyl phenol.-   1.3. Hydroquinones and alkylated hydroquinones, for example    2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,    2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol,    2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,    3,5-di-tert-butyl-4-hydroxyanisole,    3,5-di-tert-butyl-4-hydroxyphenyl stearate,    bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.-   1.4. Tocopherols, for example α-tocopherol, β-tocopherol,    γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E).-   1.5. Hydroxylated thiodiphenyl ethers, for example    2,2′-thiobis(6-tert-butyl-4-methylphenol),    2,2′-thiobis(4-octylphenol),    4,4′-thiobis(6-tert-butyl-3-methylphenol),    4,4′-thiobis(6-tert-butyl-2-methyl phenol),    4,4′-thiobis(3,6-di-sec-amylphenol),    4,4′-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide.-   1.6. Alkylidenebisphenols, for example    2,2′-methylenebis(6-tert-butyl-4-methylphenol),    2,2′-methylenebis(6-tert-butyl-4-ethylphenol),    2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol],    2,2′-methylenebis(4-methyl-6-cyclohexylphenol),    2,2′-methylenebis(6-nonyl-4-methylphenol),    2,2′-methylenebis(4,6-di-tert-butylphenol),    2,2′-ethylidenebis(4,6-di-tert-butylphenol),    2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol),    2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol],    2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol],    4,4′-methylenebis(2,6-di-tert-butylphenol),    4,4′-methylenebis(6-tert-butyl-2-methylphenol),    1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,    2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,    1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,    1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane,    ethylene glycol    bis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)-butyrate],    bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene,    bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate,    1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane,    2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-propane,    2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane,    1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methyl phenyl)pentane.-   1.7. O—, N— and S-benzyl compounds, for example    3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether,    octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate,    tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate,    tris(3,5-di-tert-butyl-4-hydroxy-benzyl)amine,    bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate,    bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide,    isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl-mercaptoacetate.-   1.8. Hydroxybenzylated malonates, for example    dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate,    di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methyl benzyl)malonate,    di-dodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,    bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.-   1.9. Aromatic hydroxybenzyl compounds, for example    1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,    1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene,    2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.-   1.10. Triazine compounds, for example    2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,    2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,    2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine,    2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine,    1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,    1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate,    2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,    1,3,5-tris(3,5-d    i-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine,    1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzypisocyanurate.-   1.11. Benzylphosphonates, for example    dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate,    diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,    dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,    dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the    calcium salt of the monoethyl ester of    3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.-   1.12. Acylaminophenols, for example 4-hydroxylauranilide,    4-hydroxystearanilide, octyl    N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.-   1.13. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid    with mono- or polyhydric alcohols, for example with methanol,    ethanol, n-octanol, i-octanol, octadecanol, a mixture of linear and    branched C₁₃-C₁₅-alkanol, 1,6-hexanediol, 1,9-nonanediol, ethylene    glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol,    diethylene glycol, triethylene glycol, pentaerythritol,    tris(hydroxylethyl)isocyanurate, N,N′-bis-(hydroxylethyl)oxamide,    3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,    trimethylolpropane,    4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.-   1.14. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic    acid with mono- or polyhydric alcohols, for example with methanol,    ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol,    1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol,    thiodiethylene glycol, diethylene glycol, triethylene glycol,    pentaerythritol, tris-(hydroxyethyl)isocyanurate,    N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,    trimethylhexanediol, trimethylolpropane,    4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;    3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane.-   1.15. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid    with mono- or polyhydric alcohols, for example with methanol,    ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol,    ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene    glycol, diethylene glycol, triethylene glycol, pentaerythritol,    tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,    3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,    trimethylolpropane,    4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octane.-   1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with    mono- or polyhydric alcohols, for example with methanol, ethanol,    octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene    glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol,    diethylene glycol, triethylene glycol, pentaerythritol,    tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,    3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,    trimethylolpropane,    4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.-   1.17. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid,    for example    N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide,    N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamide,    N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide,    N,N′-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]-propionyloxy)ethyl]oxamide    (Naugard XL-1®, supplied by Uniroyal).-   1.18. Ascorbic acid (vitamin C)-   1.19. Aminic antioxidants, for example    N,N′-di-isopropyl-p-phenylenediamine,    N,N′-di-sec-butyl-p-phenylenediamine,    N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine,    N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine,    N,N′-bis(1-methylheptyl)-p-phenylenediamine,    N,N′-dicyclohexyl-p-phenylenediamine,    N,N′-diphenyl-p-phenylenediamine,    N,N′-bis(2-naphthyl)-p-phenylenediamine,    N-isopropyl-N′-phenyl-p-phenylenediamine,    N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine,    N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine,    N-cyclohexyl-N′-phenyl-p-phenylenediamine,    4-(p-toluenesulfamoyl)diphenylamine,    N,N′-dimethyl-N,N′-di-sec-butyl-p-phenylenediamine, diphenylamine,    N-allyldiphenylamine, 4-isopropoxydiphenylamine,    N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine,    N-phenyl-2-naphthylamine, octylated diphenylamine, for example    p,p′-di-tert-octyldiphenylamine, 4-n-butylaminophenol,    4-butyrylaminophenol, 4-nonanoylaminophenol,    4-dodecanoylaminophenol, 4-octadecanoylaminophenol,    bis(4-methoxyphenyl)amine,    2,6-di-tert-butyl-4-dimethylaminomethylphenol,    2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane,    N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane,    1,2-bis[(2-methylphenyl)amino]-ethane, 1,2-bis(phenylamino)propane,    (o-tolyl)biguanide, bis[4-(1,3′-dimethylbutyl)-phenyl]amine,    tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and    dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono-    and dialkylated nonyldiphenylamines, a mixture of mono- and    dialkylated dodecyldiphenylamines, a mixture of mono- and    dialkylated isopropyl/isohexyldiphenylamines, a mixture of mono- and    dialkylated tert-butyldiphenylamines,    2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a    mixture of mono- and dialkylated    tert-butyl/tert-octylphenothiazines, a mixture of mono- and    dialkylated tert-octylphenothiazines, N-allylphenothiazine,    N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene,    N,N-bis(2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine,    bis(2,2,6,6-tetramethylpiperid-4-yl)sebacate,    2,2,6,6-tetramethylpiperidin-4-one,    2,2,6,6-tetramethylpiperidin-4-ol.-   2. UV absorbers and light stabilisers-   2.1. 2-(2′-Hydroxyphenyl)benzotriazoles, for example    2-(2′-hydroxy-5′-methylphenyl)-benzotriazole,    2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)benzotriazole,    2-(5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,    2-(2′-hydroxy-5′-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole,    2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)-5-chlorobenzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-methylphenyl)-5-chlorobenzotriazole,    2-(3′-sec-butyl-5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,    2-(2′-hydroxy-4′-octyloxyphenyl)benzotriazole,    2-(3′,5′-di-tertamyl-2′-hydroxyphenyl)benzotriazole,    2-(3′,5′-bis(α,α-dimethylbenzyl)-2′-hydroxyphenyl)benzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole,    2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)-5-chlorobenzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)-phenyl)-5-chlorobenzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)-phenyl)benzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)-benzotriazole,    2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)-benzotriazole,    2-(3′-dodecyl-2′-hydroxy-5′-methylphenyl)benzotriazole,    2-(3′-tert-butyl-2′-hydroxy-5′-(2-isooctyloxycarbonylethyl)phenylbenzotriazole,    2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol];    the transesterification product of    2-[3′-tert-butyl-5′-(2-methoxycarbonylethyl)-2′-hydroxyphenyl]-2H-benzotriazole    with polyethylene glycol 300;

where R′=3′-tert-butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl,2-[2′-hydroxy-3′-(α,α-dimethylbenzyl)-5′-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole;2-[2′-hydroxy-3′-(1,1,3,3-tetramethylbutyl)-5′-(α,α-dimethylbenzyl)phenyl]benzotriazole.

-   2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy,    4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy,    4,2′,4′-trihydroxy and 2′-hydroxy-4,4′-dimethoxy derivatives.-   2.3. Esters of substituted and unsubstituted benzoic acids, for    example 4-tert-butyl-phenyl salicylate, phenyl salicylate,    octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butyl    benzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl    3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl    3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl    3,5-di-tert-butyl-4-hydroxybenzoate,    2-methyl-4,6-di-tert-butylphenyl    3,5-di-tert-butyl-4-hydroxybenzoate.-   2.4. Acrylates, for example ethyl α-cyano-β,β-diphenylacrylate,    isooctyl α-cyano-β,β-diphenylacrylate, methyl    α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate,    butyl α-cyano-p-methyl-p-methoxycinnamate, methyl    α-carbomethoxy-p-methoxycinnamate,    N-(β-carbomethoxy-(β-cyanovinyl)-2-methylindoline and neopentyl    tetra(α-cyano-β,β-diphenylacrylate).-   2.5. Nickel compounds, for example nickel complexes of    2,2′-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol], such as the 1:1 or    1:2 complex, with or without additional ligands such as    n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel    dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g.    the methyl or ethyl ester, of    4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes    of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecylketoxime,    nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or    without additional ligands.-   2.6. Sterically hindered amines, for example    bis(2,2,6,6-tetramethyl-4-piperidyl)-sebacate,    bis(2,2,6,6-tetramethyl-4-piperidyl)succinate,    bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate,    bis(1,2,2,6,6-pentamethyl-4-piperidyl)    n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of    1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and    succinic acid, linear or cyclic condensates of    N,N′-bis(2,2,6,6-tetramethyl-4-piperidyphexamethylenediamine and    4-tert-octylamino-2,6-dichloro-1,3,5-triazine,    tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate,    tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate,    1,1′-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone),    4-benzoyl-2,2,6,6-tetramethylpiperidine,    4-stearyloxy-2,2,6,6-tetramethylpiperidine,    bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate,    3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,    bis(1-octyloxy-2,2,6,6-tetramethylpiperid-4-yl)sebacate,    bis(1-octyloxy-2,2,6,6-tetramethylpiperid-4-yl)succinate,    bis-[2,2,6,6-tetramethyl-1-(undecyloxy)-piperidin-4-yl]carbonate,    linear or cyclic condensates of    N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and    4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of    2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine    and 1,2-bis(3-aminopropylamino)ethane, the condensate of    2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine    and 1,2-bis(3-aminopropylamino)ethane,    8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,    3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione,    3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione,    a mixture of 4-hexadecyloxy- and    4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate of    N,N′-bis(2,2,6,6-tetramethyl-4-piperidyphexamethylenediamine and    4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensate of    1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine    as well as 4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No.    [136504-96-6]); a condensate of 1,6-hexanediamine and    2,4,6-trichloro-1,3,5-triazine as well as N,N-dibutylamine and    4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [192268    64-7]); N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide,    N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide,    2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane,    a reaction product of    7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane    and epichlorohydrin,    1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)-ethene,    N,N′-bis-formyl-N,N′-bis(2,2,6,6-tetramethyl-4-piperidyphexamethylenediamine,    a diester of 4-methoxymethylenemalonic acid with    1,2,2,6,6-pentamethyl-4-hydroxypiperidine,    poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane,    a reaction product of maleic acid anhydride-α-olefin copolymer with    2,2,6,6-tetramethyl-4-aminopiperidine or    1,2,2,6,6-pentamethyl-4-aminopiperidine, a mixture of oligomeric    compounds which are the formal condensation products of    N,N′-bis-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-hexane-1,6-diamine    and    2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-amino}-[1,3,5]triazine    end-capped with 2-chloro-4,6-bis-(di-n-butylamino)-[1,3,5]triazine,    a mixture of oligomeric compounds which are the formal condensation    products of    N,N′-bis-(2,2,6,6-tetramethyl-piperidin-4-yl)-hexane-1,6-diamine and    2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-piperidin-4-yl)-amino}-[1,3,5]triazine    end-capped with 2-chloro-4,6-bis-(di-n-butylamino)-[1,3,5]triazine,    2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)-N-butylamino]-6-(2-hydroxyethyl)amino-1,3,5-triazine,    1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine,    5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone,    Sanduvor (Clariant; CAS Reg. No. 106917-31-1],    5-(2-ethylhexanoyl)-oxymethyl-3,3,5-trimethyl-2-morpholinone, the    reaction product of    2,4-bis-[(1-cyclo-hexyloxy-2,2,6,6-piperidine-4-yl)butylamino]-6-chloro-s-triazine    with N,N′-bis-(3-amino-propyl)ethylenediamine),    1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazine-3-one-4-yl)amino)-s-triazine,    1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazine-3-one-4-yl)-amino)-s-triazine.-   2.7. Oxamides, for example 4,4′-dioctyloxyoxanilide,    2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide,    2,2′-didodecyloxy-5,5′-di-tert-butoxanilide,    2-ethoxy-2′-ethyloxanilide, N,N′-bis(3-dimethylaminopropyl)oxamide,    2-ethoxy-5-tert-butyl-2′-ethoxanilide and its mixture with    2-ethoxy-2′-ethyl-5,4′-di-tert-butoxanilide, mixtures of o- and    p-methoxy-disubstituted oxanilides and mixtures of o- and    p-ethoxy-disubstituted oxanilides.-   2.8. 2-(2-Hydroxyphenyl)-1,3,5-triazines, for example    2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine,    2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2,4-bis(2-hydroxy-4-propyhoxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine,    2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine,    2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,    2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,    2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,    2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine,    2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine,    2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine,    2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine,    2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]-phenyl}-4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazine.-   3. Metal deactivators, for example N,N′-diphenyloxamide,    N-salicylal-N′-salicyloyl hydrazine, N,N′-bis(salicyloyl)hydrazine,    N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine,    3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl    dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl    bisphenylhydrazide, N,N′-diacetyladipoyl dihydrazide,    N,N′-bis(salicyloyl)oxalyl dihydrazide,    N,N′-bis(salicyloyl)-thiopropionyl dihydrazide.-   4. Phosphites and phosphonites, for example triphenyl phosphite,    diphenylalkyl phosphites, phenyldialkyl phosphites,    tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl    phosphite, distearylpentaerythritol diphosphite,    tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol    diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol    diphosphite, bis(2,4-di-cumylphenyl)pentaerythritol diphosphite,    bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite,    diisodecyloxypentaerythritol diphosphite,    bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite,    bis(2,4,6-tris(tert-butyl phenyl)pentaerythritol diphosphite,    tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)    4,4′-biphenylene diphosphonite,    6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin,    bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite,    bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite,    6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin,    2,2′,2″-nitrilo-[triethyltris(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite],    2-ethylhexyl-(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite,    5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphirane.

The following phosphites are especially preferred:

Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos 168, RTM BASF),tris(nonylphenyl) phosphite,

-   5. Hydroxylamines and amine N-oxides, for example    N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine,    N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine,    N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine,    N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine,    N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine    derived from hydrogenated tallow amine or N,N-bis-(hydrogenated    rape-oil alkyl)-N-methyl-amine N-oxide.-   6. Nitrones, for example N-benzyl-alpha-phenylnitrone,    N-ethyl-alpha-methylnitrone, N-octyl-alpha-heptylnitrone,    N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone,    N-hexadecyl-alpha-pentadecylnitrone,    N-octadecyl-alpha-heptadecylnitrone,    N-hexadecyl-alpha-heptadecylnitrone,    N-ocatadecyl-alpha-pentadecylnitrone,    N-heptadecyl-alpha-heptadecylnitrone,    N-octadecyl-alpha-hexadecylnitrone, nitrone derived from    N,N-dialkylhydroxylamine derived from hydrogenated tallow amine.-   7. Thiosynergists, for example dilauryl thiodipropionate, dimistryl    thiodipropionate, distearyl thiodipropionate and pentaerythritol    tetrakis-[3-(n-lauryl)-propionic acid ester].-   8. Peroxide scavengers, for example esters of α-thiodipropionic    acid, for example the lauryl, stearyl, myristyl or tridecyl esters,    mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole,    zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol    tetrakis(β-dodecyl mercapto)propionate.-   9. Polyamide stabilizers, for example copper salts in combination    with iodides and/or phosphorus compounds and salts of divalent    manganese.-   10. Acid scavengers, for example melamine, polyvinylpyrrolidone,    dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine    derivatives, amines, polyamides, polyurethanes, alkali metal salts    and alkaline earth metal salts of higher fatty acids, for example    calcium stearate, zinc stearate, magnesium behenate, magnesium    stearate, sodium ricinoleate and potassium palmitate, antimony    pyrocatecholate and zinc pyrocatecholate.-   11. Benzofuranones and indolinones, for example those disclosed in    U.S. Pat. No. 4,325,863; U.S. Pat. No. 4,338,244; U.S. Pat. No.    5,175,312; U.S. Pat. No. 5,216,052; U.S. Pat. No. 5,252,643;    DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or    EP-A-0591102 or    3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one,    5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one,    3,3′-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]-phenyl)benzofuran-2-one],    5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one,    3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,    3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,    3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,    3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one and    3-(2-acetoxy-4-(1,1,3,3-tetramethyl-butyl)-phenyl)-5-(1,1,3,3-tetramethyl-butyl)-benzofuran-2-one.-   12. Nucleating agents, for example inorganic substances, such as    talcum, metal oxides, such as titanium dioxide or magnesium oxide,    phosphates, carbonates or sulfates of, preferably, alkaline earth    metals; organic compounds, such as mono- or polycarboxylic acids and    the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid,    diphenylacetic acid, sodium succinate or sodium benzoate; polymeric    compounds, such as ionic copolymers (ionomers), Irgaclear XT 386    (RTM BASF), 1,3:2,4-bis(3′,4′-dimethylbenzylidene)-sorbitol,    1,3:2,4-di(paramethyldibenzylidene)-sorbitol, and    1,3:2,4-di(benzylidene)sorbitol.-   13. Fillers and reinforcing agents, for example calcium carbonate,    silicates, glass fibres, glass beads, asbestos, talc, kaolin,    bentonite, mica, hydrotalcite, barium sulfate, metal oxides and    hydroxides, carbon black, graphite, wood flour and flours or fibers    of other natural products, synthetic fibers.-   14. Other additives, for example plasticisers, lubricants, rheology    additives, catalysts, flow-control agents, optical brighteners,    flameproofing agents, antistatic agents and blowing agents.

Preferred is a composition, which comprises a component a), a componentb) and as component c) a further additive.

Preferred is a composition, wherein the weight ratio of component b) tocomponent c) is from 10:1 to 1:30, in particular from 4:1 to 1:20,especially from 2:1 to 1:10, and wherein the overall amount of componentb) and component c) is below 50% by weight of component a).

Preferred is a composition, which comprises as component c) a furtheradditive selected from the group consisting of an antioxidant, an UVabsorber, a hindered amine light stabilizer, a nickel compound, a metaldeactivator, a phosphite or phosphonite, a hydroxylamine or amineN-oxide, a thiosynergist, a peroxide scavenger, a nucleating agent and afiller or reinforcing agent.

Preferred is a composition, which comprises as component c) a furtheradditive selected from the group consisting of a phosphite orphosphonite, an acid scavenger, a phenolic antioxidant and an aminicantioxidant.

Preferred is a composition, which comprises as component c) a phenolicantioxidant.

Preferred is a composition, which comprises as component c) a phenolicantioxidant, which is an ester ofβ-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

Optionally, a composition comprising a component a), a component b) anda component c) contains as component d) a second further additive.

Preferred is a composition, which comprises a component a), a componentb), as component c) a further additive and as component d) a secondfurther additive.

Preferred is a composition, wherein the weight ratio of component b) tocomponent d) is from 10:1 to 1:30, in particular from 4:1 to 1:20,especially from 2:1 to 1:10, and wherein the overall amount of componentb), component c) and component d) is below 50% by weight of componenta).

Preferred is a composition, which comprises a component a), a componentb), as component c) a further additive, which is selected from the groupconsisting of a phosphite or phosphonite, an acid scavenger, a phenolicantioxidant and an aminic antioxidant, and as component d) a secondfurther additive.

Preferred is a composition, which comprises a component a), a componentb), a component c) and a component d), wherein component c) andcomponent d) are independently from each other a phosphite orphosphonite, an acid scavenger, a phenolic antioxidant or an aminicantioxidant.

Preferred is a composition, which comprises a component a), a componentb), as component c) a phenolic antioxidant and as component d) aphosphite or phosphonite.

Preferred is a composition, which comprises a component a), a componentb), as component c) a phenolic antioxidant and as component d) an aminicantioxidant.

The above described preferences for a compound of formula I and anorganic material susceptible to oxidative, thermal or light-induceddegradation apply also to the further embodiments of the invention. Thisapplies also to the optional further additive and the optional secondfurther additive.

A further embodiment of the invention relates to a process forprotection of an organic material susceptible to oxidative, thermal orlight-induced degradation, i.e. component a), which comprises the stepof incorporation into or application onto an organic material, acompound of formula I, i.e. component b).

The incorporation or application of component b) can be carried out in aprocessing apparatus, in particular a heatable container equipped with astirrer, which can preferably be closed. A heatable container equippedwith a stirrer is for example a kneader, extruder, mixer or stirredvessel. Specific examples thereof are a single-screw extruder,contrarotating and corotating twin-screw extruder, planetary-gearextruder, ring extruder or co-kneader. It is also possible to use aprocessing apparatus, which contains at least one gas removalcompartment to which a vacuum can be applied and/or which can be setunder an atmosphere, wherein the oxygen content is low or oxygen isabsent. Component b) can be added directly into the processingapparatus.

Component b) can be incorporated or applied to at any stage ofprocessing of component a), in particular prior to or during a shapingoperation of component a) in the processing apparatus.

Component b) can be incorporated or applied in the form of a dry powder,in the form of a melt, in encapsulated form such as encapsulation in awax or polymer or in the form of a wet mixture such as a solution,dispersion or suspension for example in an inert solvent, water or oil.A dispersing or suspension agent can be present in the case of a wetmixture of component b).

Component b) can also be incorporated or applied by spraying ontocomponent a).

In case that component a) is a polymer, a further possibility forincorporation or application of component b) to component a) is additionbefore, during or directly after the polymerization of the correspondingstarting materials, e.g. monomers, of component a). For example,spraying during the deactivation of the polymerization catalysts isparticularly advantageous. If crosslinking takes place during formationof component a), incorporation or application prior to crosslinking ispreferred.

In case that component a) is a polymer, the process of incorporation orapplication is preferably a moulding process, in particular aninjection-moulding, blow-moulding, compression-moulding, roto-moulding,slush-moulding or extrusion-moulding.

Preferred is a process, wherein the incorporation or application takesplace at a temperature in the range from 150 to 340° C., in particularfrom 180° C. to 330° C., especially from 190° C. to 320° C.

Preferred is a process, wherein component b) is incorporated or appliedto in an extruder during processing of component a).

In case of a further additive, i.e. component c) or components c) andd), component b) and the further additive can be incorporated into orapplied onto component a) individually or mixed with one another. Ifdesired, the individual components can be mixed with one another beforeincorporation into component a) for example by dry blending, compaction,melting, encapsulation by a wax or polymer or as wet mixture in the formof solutions, dispersions or suspensions for example in an inertsolvent, water or oil.

Component b) and a further additive can also be added to component a) inthe form of a masterbatch (concentrate), which contains the componentb), a further additive and a masterbatch polymer. The component b) and afurther additive are incorporated into the masterbatch in aconcentration of, for example, from 1% to 40% and preferably 2% to 20%by weight of the masterbatch. The masterbatch polymer content is thedifference towards 100% by weight of the masterbatch. The masterbatchpolymer must not be necessarily the same as polymer as component a) incase the latter one is a polymer.

A further embodiment of the invention relates to an additivecomposition, which comprises

-   b) a compound of formula I, and-   c) a further additive selected from a group consisting of a    phosphite or phosphonite, an acid scavenger, a phenolic antioxidant    or an aminic antioxidant.

Preferred is a composition, wherein the weight ratio of component b) tocomponent c) is from 10:1 to 1:30, in particular from 4:1 to 1:20,especially from 2:1 to 1:10.

Preferred is an additive composition, which comprises as component d) asecond further additive.

Preferred is an additive composition, which comprises

-   b) a compound of formula I,-   c) a further additive selected from a group consisting of a    phosphite or phosphonite, an acid scavenger, a phenolic antioxidant    or an aminic antioxidant, and-   d) a second further additive selected from a group consisting of a    phosphite or phosphonite, an acid scavenger, a phenolic antioxidant    or an aminic antioxidant.

Preferred is a composition, wherein the weight ratio of component b) tocomponent c) is from 10:1 to 1:30, in particular from 4:1 to 1:20,especially from 2:1 to 1:10, and wherein the weight ratio of componentb) to component d) is from 10:1 to 1:30, in particular from 4:1 to 1:20,especially from 2:1 to 1:10.

A further embodiment of the invention relates to an article, which ismade from a composition comprising

-   a) an organic material susceptible to oxidative, thermal or    light-induced degradation, which is a polymer, and-   b) a compound of formula I.

The composition can be advantageously used for the preparation ofvarious shaped articles. Examples for such an article are:

-   I-1) Floating devices, marine applications, pontoons, buoys, plastic    lumber for decks, piers, boats, kayaks, oars, and beach    reinforcements.-   I-2) Automotive applications, in particular bumpers, dashboards,    battery, rear and front linings, moldings parts under the hood, hat    shelf, trunk linings, interior linings, air bag covers, electronic    moldings for fittings (lights), panes for dashboards, headlamp    glass, instrument panel, exterior linings, upholstery, automotive    lights, head lights, parking lights, rear lights, stop lights,    interior and exterior trims; door panels; gas tank; glazing front    side; rear windows; seat backing, exterior panels, wire insulation,    profile extrusion for sealing, cladding, pillar covers, chassis    parts, exhaust systems, fuel filter/filler, fuel pumps, fuel tank,    body side mouldings, convertible tops, exterior mirrors, exterior    trim, fasteners/fixings, front end module, glass, hinges, lock    systems, luggage/roof racks, pressed/stamped parts, seals, side    impact protection, sound deadener/insulator and sunroof.-   I-3) Road traffic devices, in particular sign postings, posts for    road marking, car accessories, warning triangles, medical cases,    helmets, tires.-   I-4) Devices for plane, railway, motor car (car, motorbike, trucks)    including furnishings.-   I-5) Devices for space applications, in particular rockets and    satellites, e.g. reentry shields.-   I-6) Devices for architecture and design, mining applications,    acoustic quietized systems, street refuges, and shelters.-   II-1) Appliances, cases and coverings in general and    electric/electronic devices (personal computer, telephone, portable    phone, printer, television-sets, audio and video devices), flower    pots, satellite TV bowl, and panel devices.-   II-2) Jacketing for other materials such as steel or textiles.-   II-3) Devices for the electronic industry, in particular insulation    for plugs, especially computer plugs, cases for electric and    electronic parts, printed boards, and materials for electronic data    storage such as chips, check cards or credit cards.-   II-4) Electric appliances, in particular washing machines, tumblers,    ovens (microwave oven), dish-washers, mixers, and irons.-   II-5) Covers for lights (e.g. street-lights, lamp-shades).-   II-6) Applications in wire and cable (semi-conductor, insulation and    cable-jacketing).-   II-7) Foils for condensers, refrigerators, heating devices, air    conditioners, encapsulating of electronics, semi-conductors, coffee    machines, and vacuum cleaners.-   III-1) Technical articles such as cogwheel (gear), slide fittings,    spacers, screws, bolts, handles, and knobs.-   III-2) Rotor blades, ventilators and windmill vanes, solar devices,    swimming pools, swimming pool covers, pool liners, pond liners,    closets, wardrobes, dividing walls, slat walls, folding walls,    roofs, shutters (e.g. roller shutters), fittings, connections    between pipes, sleeves, and conveyor belts.-   III-3) Sanitary articles, in particular shower cubicles, lavatory    seats, covers, and sinks.-   III-4) Hygienic articles, in particular diapers (babies, adult    incontinence), feminine hygiene articles, shower curtains, brushes,    mats, tubs, mobile toilets, tooth brushes, and bed pans.-   III-5) Pipes (cross-linked or not) for water, waste water and    chemicals, pipes for wire and cable protection, pipes for gas, oil    and sewage, guttering, down pipes, and drainage systems.-   III-6) Profiles of any geometry (window panes) and siding.-   III-7) Glass substitutes, in particular extruded or co-extruded    plates, glazing for buildings (monolithic, twin or multiwall),    aircraft, schools, extruded sheets, window film for architectural    glazing, train, transportation, sanitary articles, and greenhouse.-   III-8) Plates (walls, cutting board), extrusion-coating    (photographic paper, tetrapack and pipe coating), silos, wood    substitute, plastic lumber, wood composites, walls, surfaces,    furniture, decorative foil, floor coverings (interior and exterior    applications), flooring, duck boards, and tiles.-   III-9) Intake and outlet manifolds.-   III-10) Cement-, concrete-, composite-applications and covers,    siding and cladding, hand rails, banisters, kitchen work tops,    roofing, roofing sheets, tiles, and tarpaulins.-   IV-1) Plates (walls and cutting board), trays, artificial grass,    astroturf, artificial covering for stadium rings (athletics),    artificial floor for stadium rings (athletics), and tapes.-   IV-2) Woven fabrics continuous and staple, fibers (carpets/hygienic    articles/geotextiles/monofilaments; filters; wipes/curtains    (shades)/medical applications), bulk fibers (applications such as    gown/protection clothes), nets, ropes, cables, strings, cords,    threads, safety seat-belts, clothes, underwear, gloves; boots;    rubber boots, intimate apparel, garments, swimwear, sportswear,    umbrellas (parasol, sunshade), parachutes, paraglides, sails,    “balloon-silk”, camping articles, tents, airbeds, sun beds, bulk    bags, and bags. Non-woven fabrics such as medical fabrics and    related apparel, industrial apparel, outdoor fabrics, in-home    furnishing and construction fabrics.-   IV-3) Membranes, insulation, covers and seals for roofs, tunnels,    dumps, ponds, dumps, walls roofing membranes, geomembranes, swimming    pools, curtains (shades)/sun-shields, awnings, canopies, wallpaper,    food packing and wrapping (flexible and solid), medical packaging    (flexible & solid), airbags/safety belts, arm- and head rests,    carpets, centre console, dashboard, cockpits, door, overhead console    module, door trim, headliners, interior lighting, interior mirrors,    parcel shelf, rear luggage cover, seats, steering column, steering    wheel, textiles, and trunk trim.-   V) Films (packaging, dump, laminating, agriculture and horticulture,    greenhouse, mulch, tunnel, silage), bale wrap, swimming pools, waste    bags, wallpaper, stretch film, raffia, desalination film, batteries,    and connectors.-   VI-1) Food packing and wrapping (flexible and solid), bottles.-   VI-2) Storage systems such as boxes (crates), luggage, chest,    household boxes, pallets, shelves, tracks, screw boxes, packs, and    cans.-   VI-3) Cartridges, syringes, medical applications, containers for any    transportation, waste baskets and waste bins, waste bags, bins, dust    bins, bin liners, wheely bins, container in general, tanks for    water/used water/chemistry/gas/oil/gasoline/diesel; tank liners,    boxes, crates, battery cases, troughs, medical devices such as    piston, ophthalmic applications, diagnostic devices, and packing for    pharmaceuticals blister.-   VII-1) Extrusion coating (photo paper, tetrapack, pipe coating),    household articles of any kind (e.g. appliances, thermos    bottle/clothes hanger), fastening systems such as plugs, wire and    cable clamps, zippers, closures, locks, and snap-closures.-   VII-2) Support devices, articles for the leisure time such as sports    and fitness devices, gymnastics mats, ski-boots, inline-skates,    skis, big foot, athletic surfaces (e.g. tennis grounds); screw tops,    tops and stoppers for bottles, and cans.-   VII-3) Furniture in general, foamed articles (cushions, impact    absorbers), foams, sponges, dish clothes, mats, garden chairs,    stadium seats, tables, couches, toys, building kits    (boards/figures/balls), playhouses, slides, and play vehicles.-   VII-4) Materials for optical and magnetic data storage.-   VII-5) Kitchen ware (eating, drinking, cooking, storing).-   VII-6) Boxes for CD's, cassettes and video tapes; DVD electronic    articles, office supplies of any kind (ball-point pens, stamps and    ink-pads, mouse, shelves, tracks), bottles of any volume and content    (drinks, detergents, cosmetics including perfumes), and adhesive    tapes.-   VII-7) Footwear (shoes/shoe-soles), insoles, spats, adhesives,    structural adhesives, food boxes (fruit, vegetables, meat, fish),    synthetic paper, labels for bottles, couches, artificial joints    (human), printing plates (flexographic), printed circuit boards, and    display technologies.-   VII-8) Devices of filled polymers (talc, chalk, china clay (kaolin),    wollastonite, pigments, carbon black, TiO₂, mica, nanocomposites,    dolomite, silicates, glass, asbestos).

Preferred is an article, which is a film, pipe, profile, bottle, tank,container or fiber.

Preferred is an article, which is moulded. In particular, the mouldingis effected by injection, blow, compression, roto-moulding,slush-moulding or extrusion.

A further embodiment to the invention relates to the use of a compoundof formula I, i.e. component b), for stabilizing an organic materialsusceptible to oxidative, thermal or light-induced degradation, i.e.component a), against degradation by oxidation, heat or light.

Preferred is the use of component b) for stabilizing a polyurethane foamagainst scorching.

Processing of a component a) is characterized as short-term exposure ofthe component a) to heat, for example to a temperature in the range of150° C. to 340° C., during the time of processing of component a). Thetime of processing is short in comparison to for example the possibletime of usage. Usage takes typically place at a temperature, for example0° C. to 50° C., which is below the temperature during processing.

Preferred is the use of component b) for stabilizing a component a)against oxidative or thermal degradation during processing.

Compounds of formula I are partly new and partly known. Severalsynthetic routes to known compounds of formula I are described inliterature.

A further embodiment of the invention relates to a compound of formula I

wherein

-   when n is 1-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃) or —SO₂-phenyl;-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl),    3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl),    1,4,7-triazaheptane-1,4,7-tricarbonyl,    1,4,8-triazaoctane-1,4,8-tricarbonyl or    1,5,9-triazanonane-1,5,9-tricarbonyl;-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl),    1,4,7,10-tetraazadecane-1,4,7,10-tetracarbonyl,    1,4,8,11-tetraazaundecane-1,4,8,11-tetracarbonyl or    1,5,8,12-tetraazadodecane-1,5,8,12-tetracarbonyl;-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,    which is substituted by a hydroxyl group,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms,    hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,    C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a compound of formula I, wherein

-   when n is 1-   A is —C(═O)—OR′₁ or —C(═O)—N(R′₂)(R′₃);-   when n is 2-   A is —C(═O)—O—Z₁—O—C(═O)—, —O(═O)—N(R″₁)—Z₂—N(R″₂)—O(═O)— or    piperazine-N,N′-biscarbonyl;-   when n is 3-   A is C₃-C₁₂-alkane-tri-(oxycarbonyl);-   when n is 4-   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl);-   n is 1, 2, 3 or 4;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,    which is substituted by a hydroxyl group,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;-   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl;-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms,    hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and-   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,    C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is    interrupted by one or more oxygen atoms,    3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

A further embodiment of the invention relates to a synthesis method fora compound of formula I

wherein

-   n is 1;-   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃);-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen;-   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,    C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to    three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or    tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which    is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which    is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is    interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;-   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,    C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or    substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,    C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₈-alkyl,    which is substituted by one hydroxyl group,    2,2,6,6-tetramethylpiperidine-4-yl,    1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidin-4-yl or    1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃    form together with the nitrogen atom to which they are attached a    5-, 6- or 7-membered saturated heterocycle;

which comprises the step of reacting a compound of formula II

wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ have the meaning as    indicated above; with a compound of formula III

wherein

-   R_(e) is C₁-C₈-alkyl;-   Y is OR′, or N(R′₂)(R′₃); and-   R′₁, R′₂ and R′₃ have the meaning as indicated above; in the    presence of an organic or inorganic base and a solvent.

Preferably, R_(e) is C₁-C₄-alkyl, in particular methyl or ethyl.

Preferably, the organic base is sodium methanolate or sodium ethanolate.

Preferably, the solvent is methanol or ethanol, in particular methanol.

Preferably, the temperature during the synthesis is in the range of 0°C. to 240° C.

A further embodiment of the invention relates to a synthesis method fora compound of formula I

wherein

-   n is 2;-   A is —C(═O)—O—Z₁—O—C(═O)—;-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from    each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or    halogen; and-   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,    C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),    C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is    substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which    is interrupted by one or more oxygen atoms,    hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is    interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,    4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or    1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl;

which comprises the step of reacting a compound of formula Ia

wherein

-   R_(ee) is C₁-C₈-alkyl; and-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ have the meaning as    indicated above;

with a compound of formula VHO—Z₁—OH  (V)

wherein Z₁ has the meaning as indicated above;

in the presence of a solvent.

Preferably, the temperature during the synthesis is in the range of 70°C. to 240° C.

Preferably, R_(e) is C₁-C₄-alkyl, in particular methyl or ethyl.

Preferably, the solvent has a boiling point above the boiling point ofR_(ee)—OH. Preferably, the solvent is free of a hydroxyl group. Forexample, the solvent is toluene, xylene or dichlorobenzene.

Preferably, the synthesis is conducted under vacuum.

Preferably, a transesterification catalyst is added.

The following examples illustrate further the invention without limitingit.

EXAMPLE 1 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid methylester (201)

45 g benzoin (=2-hydroxy-1,2-bis-phenyl-ethanone; 212 mmol) and 70 gdimethyl malonate (530 mmol) are dissolved under reflux in 75 mLmethanol. 22.9 g sodium methoxide (424 mmol) is dissolved in 1250 mLmethanol and added. The mixture is stirred at 40° for 1 h and thenacidified with diluted aqueous hydrochloric acid to pH 3-4. Theprecipitate is filtered off, washed with water and afterwards withmethanol and dried in vacuo. 50.8 g of compound (201) are obtained(81%); mp. 113-115°.

EXAMPLE 24,5-Bis-(4-methoxy-phenyl)-2-oxo-2,5-dihydro-furan-3-carboxylic acidmethyl ester (202)

10 g anisoin (=2-hydroxy-1,2-bis-(4-methoxy-phenyl)-ethanone; 36.7 mmol)and 12.13 g dimethyl malonate (91.8 mmol) are dissolved in 70 mLmethanol under reflux. 1.68 g sodium (73.4 mmol) is dissolved in 70 mLmethanol and added. The mixture is refluxed for 18 h, then cooled to 25°and acidified with diluted aqueous hydrochloric acid. The resultingmixture is extracted with ethyl acetate/toluene. The organic phases arewashed with water, dried over magnesium sulfate, and evaporated todryness. Recrystallization from methanol yields 5.61 g of compound (202)(41%); mp. 107-109°.

EXAMPLE 3 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid amide(203)

10 g benzoin (47 mmol) and 11 g methyl malonamate (94 mmol) aredissolved in 100 mL methanol at reflux. 5.07 g sodium methoxide (94mmol) is dissolved in 40 mL methanol and added. The mixture is refluxedfor 1 h. The resulting suspension is acidified at 25° with dilutedaqueous hydrochloric acid to pH 3-4 and the precipitate is filtered off,dried and recrystallized from toluene. 10.1 g of compound (203) isobtained (77%); mp. 125-127°.

EXAMPLE 4 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidoctylamide (204)

1 g benzoin (4.7 mmol) and 1.6 g of compound (401) (7 mmol) aredissolved in 5 mL methanol. 0.63 g of sodium methoxide (9.4 mmol) in 5mL methanol is added and the mixture is refluxed for 2 h. The mixture isacidified with diluted aqueous hydrochloric acid to pH 3-4 and extractedtwice with ethyl acetate. The organic phases are washed with water,dried over sodium sulfate and evaporated to dryness. 1.25 g of compound(204) is obtained as vicous oil (68%).

EXAMPLE 5 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidcyclohexylamide (205)

In analogy to example 4, benzoin and compound (402) are reacted andcompound (205) is obtained (49%); mp. 151-153° C.

EXAMPLE 6 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid(1,1,3,3-tetramethyl-butyl)-amide (206)

In analogy to example 4, benzoin and compound (403) are reacted andcompound (206) is obtained (64%); mp. 110-111° C.

EXAMPLE 7 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidbenzylamide (207)

In analogy to example 4, benzoin and compound (404) are reacted andcompound (207) is obtained (54%); mp. 173-175° C.

EXAMPLE 8 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-amide (208)

In analogy to example 4, benzoin and compound (405) are reacted andcompound (208) is obtained (99%) as waxy solid; mp. 79-85° C.

EXAMPLE 9 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic aciddibutylamide (209)

7.4 g benzoin (35 mmol) and 12 g of compound (406) (52 mmol) aredissolved in 80 mL methanol at reflux. 3.78 g sodium methoxide (70 mmol)is dissolved in 40 mL methanol and added. The reaction mixture isrefluxed for 2.5 h. Then, the mixture is acidified with diluted aqueoushydrochloric acid to pH 3-4 and extracted with diethyl ether. Theorganic phase is separated, washed with water, dried over sodiumsulfate, and evaporated in vacuo. 13.6 g of compound (209) is obtained(99%) as a slightly yellow liquid; MS (liquid chromatography/massspectroscopy atmospheric pressure chemical ionisation (positive mode)(=LC/MS APCI (pos. mode)): 392 ([MH]⁺).

EXAMPLE 10 3-(Morpholine-4-carbonyl)-4,5-diphenyl-5H-furan-2-one (210)

In analogy to example 9, benzoin and compound (407) are reacted andcompound (210) is obtained (92%); mp. 204-206° C.

EXAMPLE 11 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidphenylamide (211)

In analogy to example 9, benzoin and compound (408) are reacted andcompound (211) is obtained (58%); mp. 148-150° C.

EXAMPLE 12 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid ethylester (212)

5 g of compound (201) (17 mmol) is dissolved in 50 mL ethanol and heatedto reflux with a oilbath temperature of 100° C. A mixture of ethanol andmethanol is distilled off. Ethanol is replaced regularly under thesedistillation conditions. After 8 h of distilling, the turnover iscomplete and the solution is evaporated in vacuo. 4.77 g of compound(212) is obtained (91%) as a viscous oil.

EXAMPLE 13 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid propylester (213)

In analogy to example 12, compound (201) and 1-propanol are reacted andcompound (213) is obtained (98%) as a liquid.

EXAMPLE 14 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid pentylester (214)

In analogy to example 12, compound (201) and 1-pentanol are reacted andcompound (214) is obtained (83%) as liquid.

EXAMPLE 15 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid1-methoxy-2,2,6,6-tetramethyl-piperidin-4-yl ester (215)

In analogy to example 12 and with tetralin employed as co-solvent,compound (201) and 1-methoxy-2,2,6,6-tetramethyl-piperidin-4-ol arereacted and compound (215) is obtained (37%); mp. 143-146° C.

EXAMPLE 16 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidcyclohexyl ester (216)

In analogy to example 12, compound (201) and cyclohexanol are reactedand compound (216) is obtained (82%); mp. 139-142° C.

EXAMPLE 17 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid benzylester (217)

In analogy to example 12, compound (201) and benzyl alcohol are reactedand compound (217) is obtained (73%); mp. 111-114° C.

EXAMPLE 18 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidisopropyl ester (218)

In analogy to example 12, compound (201) and isopropanol are reacted andcompound (218) is obtained (85%); mp. 120-122° C.

EXAMPLE 19 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acidtert-butyl ester (219)

In analogy to example 12, compound (201) and 2-methyl-2-propanol arereacted and compound (219) is obtained (75%); mp. 109-111° C.

EXAMPLE 20 Bis-(2-oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid)cyclohexane-1,4-diyl diester (220)

50 g of compound (201) (170 mmol) is melted at 140°. 10 gcyclohexan-1,4-diol (mixture of cis- and trans-isomer, 87 mmol) is addedand followed by addition of 20 mL o-dichlorobenzene. The resultingmethanol is distilled off at oil bath temperature of 190°. After 6 h themixture is cooled to room temperature and 50 mL toluene is added. Theprecipitate is filtered off, washed with toluene, then hexane, and driedin vacuo. 18.61 g of compound (220) as a mixture of isomers is obtained(33%); mp. 237-240° C.

EXAMPLE 21 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid (221)

15 g of compound (219) (44 mmol) is stirred into 100 mL of sulfuric acid(96%) at 25°. After 1 h, the solution is added dropwise to a mixture ofice-water and dichloromethane under stirring. The organic phases arewashed with water, then brine, dried over sodium sulfate, and evaporatedto dryness. Recrystallization from chloroform yields 5.77 g of compound(221) (46%); mp. 116-117°.

EXAMPLE 22 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carbonitrile (222)

Compound (222) is prepared according to J. A. McRae and A. L. Kuehner,Journal of the American Chemical Society, 1930, 52, 3377-3382.

EXAMPLE 234,5-Bis-(4-methoxy-phenyl)-2-oxo-2,5-dihydro-furan-3-carbonitrile (223)

Compound (223) is prepared in analogy to compound (222).

EXAMPLE 24 4,5-Diphenyl-5H-furan-2-one (224)

Compound (224) is a known compound.

10 g benzoin (47 mmol) and 37.6 g dimethyl malonate (235 mmol) areheated to 170° C. for 2 h. After cooling to room temperature, thereaction mass is triturated with hexane, the precipitate is filtered offand dried in vacuum. 6.7 g of compound (224) is obtained (60.5%) aswhite crystals; mp. 147149° C.

EXAMPLE 25 3-Benzenesulfonyl-4,5-diphenyl-5H-furan-2-one (225)

In analogy to example 2, 2.92 g benzoin (13 mmol) and 5.0 gphenylsulfonyl acetic acid methyl ester (20 mmol) are reacted. 4.02 g ofcompound (225) is obtained (76%) as yellow oil; MS (LC/MS APCI (pos.mode)): 377 ([MH]⁺).

EXAMPLE 26 3,4,5-Triphenyl-5H-furan-2-one (226)

Compound (226) is a known compound.

40 g benzoin (=2-hydroxy-1,2-bis-phenyl-ethanone; 188 mmol) and 84.9 gmethylphenyl acetate (565 mmol) are dissolved under reflux in 200 mLmethanol. 30.5 g sodium methoxide (565 mmol) is dissolved in 100 mLmethanol and added. The mixture is stirred at 65° C. for 15 h and thenacidified with diluted aqueous hydrochloric acid to pH 3-4. Theprecipitate is filtered off, washed with water and afterwards withmethanol and dried in vacuo. 44.4 g of compound (226) are obtained,which are recrystallized from ethyl acetate/hexane to obtain 29.9 g(51%) of compound (226) as white crystals; mp. 120-122° C., MS (LC/MSAPCI (pos. mode)): 313 ([MH]⁺).

EXAMPLE 27 N-Octyl-malonamic acid methyl ester (401)

13.2 g dimethyl malonate (100 mmol) and 6.45 g octylamine (50 mmol) areheated to 125° C. and resulting methanol is distilled off. After 2.5 hat 125°, the reaction mixture is cooled to room temperature, the sideproduct (bisamide) is precipitated with methanol and removed byfiltration. The filtrate is concentrated in vacuo. 7.41 g of compound(401) is obtained (65%) as a liquid; pure by ¹H-NMR.

EXAMPLE 28 N-Cyclohexyl-malonamic acid methyl ester (402)

In analogy to example 27, compound (402) is obtained (64%); mp. 77-78°C.

EXAMPLE 29 N-(1,1,3,3-Tetramethyl-butyl)-malonamic acid methyl ester(403)

In analogy to example 27, compound (403) is obtained (97%); mp. 74-75°C.

EXAMPLE 30 N-Benzyl-malonamic acid methyl ester (404)

In analogy to example 27, compound (404) is obtained (63%); mp. 51-54°C.

EXAMPLE 31 N-(2,2,6,6-Tetramethyl-1-propoxy-piperidin-4-yl)-malonamicacid methyl ester (405)

In analogy to example 27, compound (405) is obtained (55%) assemi-crystalline/waxy material.

EXAMPLE 32 N,N-Dibutyl-malonamic acid methyl ester (406)

10 g methyl malonyl monochloride (=chlorocarbonyl-acetic acid methylester; 73 mmol) and 20.8 g dibutylamine (161 mmol, in excess) arereacted in diethylether at 0° C. Compound (406) is obtained (78%) asyellow, viscous oil.

EXAMPLE 33 3-Morpholin-4-yl-3-oxo-propionic acid methyl ester (407)

In analogy to example 32, compound (407) is obtained (69.5%) as orange,viscous oil.

EXAMPLE 34 N-Phenyl-malonamic acid methyl ester (408)

In analogy to example 32, compound (408) is obtained (89.8%) as whitecrystals.

EXAMPLE 35 Stabilization of Polyol

The oxidation resistance of polyol is determined by differentialscanning calorimetry (DSC). A sample is heated starting at 50° C. with aheating rate of 5° C./min under oxygen until 200° C. are reached. Theappearance of an exothermic peak indicates the beginning of athermo-oxidative reaction. The temperature at the onset of theexothermic peak is noted. A better stabilized sample is characterized bya higher temperature for the onset.

100 parts of Lupranol 2084 (RTM BASF; polyol) are admixed with 0.45parts of a stabilizer composition, which consists of Irganox 1135 (RTMBASF; 0.32 parts based on 100 parts of polyol), Irganox 5057 (RTM BASF;0.10 parts based on 100 parts of polyol) and a compound of formula Iaccording to the invention (0.03 parts based on 100 parts of polyol). Incomparative example 35a), no stabilizer composition is added.

Lupranol 2084 (RTM BASF) is a trifunctional polyether polyol, whichcontains predominantly secondary hydroxyl groups and which possess ahydroxyl number 48 mg KOH/g, a water content less than 0.1% and an acidnumber less than 0.06 mg KOH/g.

Irganox 1135 (RTM BASF) is a phenolic antioxidant and contains3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionic acid iso-octyl ester asdepicted:

Irganox 5057 (RTM BASF) is an aminic antioxidant and is a technicalmixture obtained by the reaction of diphenylamine with diisobutylene,comprising

-   -   α) diphenylamine;    -   β) 4-tert-butyldiphenylamine;    -   γ) compounds of the group        -   i) 4-tert-octyldiphenylamine,        -   ii) 4,4′-di-tert-butyldiphenylamine,        -   iii) 2,4,4′-tris-tert-butyldiphenylamine,    -   δ) compounds of the group        -   i) 4-tert-butyl-4′-tert-octyldiphenylamine,        -   ii) o,o′, m,m′, or p,p′-di-tert-octyldiphenylamine,        -   iii) 2,4-di-tert-butyl-4′-tert-octyldiphenylamine,    -   ε) compounds of the group    -   i) 4,4′-di-tert-octyldiphenylamine,    -   ii) 2,4-di-tert-octyl-4′-tert-butyldiphenylamine, and

wherein not more than 5% by weight of component α), 8 to 15% by weightof component β), 24 to 32% by weight of component γ), 23 to 34% byweight of component δ) and 21 to 34% by weight of component ε) arepresent.

TABLE 1 temperature of onset example tested sample [° C.] 35a)^(a)) 100parts polyol without 132 stabilizer composition 100 parts polyol with0.45 parts stabilizer composition containing compound 35b)^(b)) (201)188 35c)^(b)) (202) 193 35d)^(b)) (205) 193 35e)^(b)) (206) 19735f)^(b)) (207) 194 35g)^(b)) (214) 194 35h)^(b)) (215) 195 35i)^(b))(216) 193 35j)^(b)) (218) 191 35k)^(b)) (219) 192 35l)^(b)) (220) 19235m)^(b)) (222) 191 35n)^(b)) (223) 189 35o)^(b)) (224) 190^(a))comparative ^(b))according to the invention

EXAMPLE 36 Stabilization of Polyether/Polyurethane Soft Foam

Preparation of Polyether/Polyurethane Soft Foam:

0.71 g of a stabilizer composition (0.45 parts based on 100 parts ofpolyol), which consists of Irganox 1135 (RTM BASF; phenolic antioxidantas described at example 35; 0.32 parts based on 100 parts of polyol),Irganox 5057 (RTM BASF; aminic antioxidant as described at example 35;0.10 parts based on 100 parts of polyol) and a compound of formula Iaccording to the invention (0.03 parts based on 100 parts of polyol), isdissolved in 157.1 g Lupranol 2084 (RTM BASF; polyol as described inexample 35). In case of comparative examples 36a) and 36f), nostabilizer composition is added. 9.84 g of a solution consisting of 1.88g Tegostab BF 2370 (RTM Evonik Industries; surfactant based onpolysiloxane), 0.24 g Tegoamin 33 (RTM Evonik Industries; generalpurpose catalyst based on triethylene diamine) and 7.7 g of deionizedwater are added and the reaction mixture is stirred vigorously for 10seconds at 2600 rpm. 0.31 g Kosmos 29 (RTM Evonik Industries; gellingcatalyst based on stannous octoate) is then added and the reactionmixture is again stirred vigorously for 18 seconds at 2600 rpm. 92.19 gof Lupranat T80 (RTM BASF; toluene-2,4- and toluoylene-2,6-diisocyanatemixture) is then added with continuous stirring for 5 to 7 seconds at2600 rpm. The mixture is then poured into a 20×20×20 cm cake-box and anexothermic foaming reaction takes place as indicated by an increase oftemperature. The foam blocks are cooled and stored at room temperaturefor 24 hours.

All prepared foam blocks show a comparable initial white colour.

Anti-Scorch Testing

Scorch resistance is determined by static heat aging, i.e. staticalu-block test. The foam blocks are cut into thin tubes (2 cm thick, 1.5cm in diameter). From each foam block, a thin tube is taken as foamsample. The foam sample is heated in an aluminum block.

The temperature is kept at 180° C. for 30 minutes.

The scorch resistance is assessed by measuring the colour of the foamsample after aging. The measured colour is reported in terms ofYellowness Index (YI) determined on the foam sample in accordance withthe ASTM 1926-70 Yellowness Test. Low YI values denote littlediscoloration and high YI values severe discoloration of the samples.The whiter a foam sample remains, the better the foam sample isstabilized.

TABLE 2 Yellowness index after 30 minutes example employed polyolcomponent at 180° C. 36a)^(a)) 100 parts polyol without stabilizer 26composition 100 parts polyol with 0.45 parts stabilizer compositioncontaining compound 36b)^(b)) (201) 1 36c)^(b)) (222) 2 36d)^(b)) (223)1 36e)^(b)) (224) 3 Footnotes are listed at table 1.

TABLE 3 Yellowness index after 30 minutes example employed polyolcomponent at 180° C. 36f)^(a)) 100 parts polyol without stabilizer 25composition 100 parts polyol with 0.45 parts stabilizer compositioncontaining compound 36g)^(b)) (202) 2 36h)^(b)) (205) 1 36i)^(b)) (206)1 36j)^(b)) (207) 1 36k)^(b)) (214) 2 36l)^(b)) (215) 1 36m)^(b)) (216)2 36n)^(b)) (218) 2 36o)^(b)) (219) 2 36p)^(b)) (220) 2 Footnotes arelisted at table 1.

EXAMPLE 37 Stabilization of Polypropylene

Method 1:

The employed mini-extruder, which is commercially available from DSM,enables a flow of the melted polymer in a circle, i.e. two screws in atwin-screw arrangement press the melted polymer to the outlet, which isconnected to the inlet zone of the extruder. The temperature of thesteel barrel of the mini-extruder can be regulated and the inlet zone ofthe extruder can be purged with a gas, which allows the removal ofentrapped air originating from the loading of the polymer sample.Furthermore, a sensor determines the force, which is exerted by themelted polymer onto the barrel during rotation of the two screws. Achange in the viscosity of the melted polymer leads to a change of theforce.

The steel housing of the extruder is set at a temperature of 280° C. andthe inlet zone is set under a nitrogen flow of 20 mL/min. At a screwspeed of 50 rpm, 9 g of a mixture, which consists of 8.955 g of a pipegrade polypropylene random copolymer (99.95% of the overall mixture) and0.0045 g of a compound according to the invention (0.05% of the overallmixture) are loaded. In case of comparative example 37a), a compoundaccording to the invention is not added. Said polypropylene randomcopolymer itself already contains 0.2%tetrakis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionyloxymethyl]-methane,0.2% 1,3,5-tri-(2,6-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,0.1% tris-(2,4-di-tert-butylphenyl)phosphite and 0.05% calcium stearate.

Tetrakis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionyloxymethyl]methaneis a phenolic antioxidant, which is contained for example in Irganox1010 (RTM BASF), as depicted:

1,3,5-Tri-(2,6-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene is aphenolic antioxidant, which is contained for example in Irganox 1330(RTM BASF), as depicted:

Tris-(2,4-di-tert-butylphenyl)phosphite is a phosphite stabilizer, whichis contained for example in Irgafos 168 (RTM BASF), as depicted:

After loading, the screw speed is set to 100 rpm and the force exertedon the barrel is recorded. The test is conducted for 10 min undernitrogen at a flow rate of 20 mL/min. After a short period, a steadydecrease of the force is recorded. The decrease of the force isquantified as slope of the force-to-time curve, wherein the slope iscalculated between the time period of 7 and 10 minutes. The curve israther linear during said period. The decrease of the force with time istaken as degree of melt-degradation of the polymer sample.

Desired is a minimum of degradation, which is expressed by a small valuefor the slope of the curve. No degradation would mean zero slope.

The results are shown in table 4.

Method 2: Multiple Pass Extrusion Test

2500 g of polypropylene random copolymer (as described under method 1including the mentioned additives) is blended with 1.25 g of a compoundaccording to the invention and compounded under nitrogen at 220° C. witha twin screw extruder. In case of comparative example 37t), a compoundaccording to the invention is not added. The pellets are extruded 5 moretimes at 280° C. under air. The melt flow of the pellets after the5^(th) extrusion is measured at 230° C. with a weight of 5 kg accordingto ISO 1133:1997.

A very small change of the melt index indicates less degradation.Ideally, there would be no change in melt flow.

The results are shown in table 5.

TABLE 4 example tested composition method 1 [slope] 37a)^(a)) withoutaddition of a compound according −0.8 to the invention with compound37b)^(b)) (201) −0.2 37c)^(b)) (202) −0.45 37d)^(b)) (205) −0.4837e)^(b)) (206) −0.54 37f)^(b)) (207) −0.47 37g)^(b)) (209) −0.4237h)^(b)) (210) −0.38 37i)^(b)) (211) −0.4 37j)^(b)) (214) −0.5637k)^(b)) (216) −0.4 37l)^(b)) (218) −0.44 37m)^(b)) (219) −0.4337n)^(b)) (220) −0.31 37o)^(b)) (221) −0.34 37p)^(b)) (222) −0.1937q)^(b)) (223) −0.14 37r)^(b)) (224) −0.17 37s)^(b)) (226) −0.09Footnotes are listed at table 1.

TABLE 5 method 2 [melt flow (5 kg/ example tested composition 230° C.)after 5th extrusion] 37t)^(a)) without addition of a compound 3.35according to the invention with compound 37u)^(b)) (201) 2.6 37v)^(b))(222) 2.2 37w)^(b)) (224) 2.6 Footnotes are listed at table 1.

The invention claimed is:
 1. A composition, which comprises a) apolyolefin; and b) a compound of formula I

wherein n is 1, A is phenyl which is substituted by one or moreC₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen; and R₁, R₂, R₃,R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H.
 2. A composition according toclaim 1, wherein in the compound of formula I, A is phenyl which issubstituted by one to three C₁-C₈-alkyl or C₁-C₄-alkoxy.
 3. Acomposition according to claim 1, wherein component b) is contained inan amount of 0.0005% to 10% based on the weight of component a).
 4. Acomposition according to claim 1, which comprises c) a further additive.5. A composition according to claim 4, which comprises c) an additiveselected from the group consisting of a phosphite, a phosphonite, anacid scavenger, a phenolic antioxidant and an aminic antioxidant.
 6. Acomposition according to claim 4, wherein the weight ratio of b) to c)is from 4:1 to 1:20.
 7. A composition according to claim 5, whichcomprises d) a second further additive selected from the groupconsisting of a phosphite, a phosphonite, an acid scavenger, a phenolicantioxidant and an aminic antioxidant.
 8. A process for protection of apolyolefin, which process comprises incorporating into or applying ontothe organic material a compound of formula I

wherein n is 1, A is phenyl which is unsubstituted or substituted by oneor more C₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyle or halogen; R₁, R₂,R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H.